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Synthesis and Anticancer Activity of ( R , S )‐9‐(2,3‐Dihydro‐1,4‐Benzoxathiin‐3‐ylmethyl)‐9 H ‐Purines
Author(s) -
DíazGavilán Mónica,
ConejoGarcía Ana,
CruzLópez Olga,
Núñez María C.,
ChoquesilloLazarte Duane,
GonzálezPérez Josefa M.,
RodríguezSerrano Fernando,
Marchal Juan A.,
Aránega Antonia,
Gallo Miguel A.,
Espinosa Antonio,
Campos Joaquín M.
Publication year - 2008
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200700180
Subject(s) - chemistry , stereochemistry , purine metabolism , purine , ring (chemistry) , biochemistry , enzyme , organic chemistry
A series of eleven 2‐ and 6‐substituted ( R,S )‐9‐(2,3‐dihydro‐1,4‐benzoxathiin‐3‐ylmethyl)‐9 H ‐purine derivatives was obtained by applying a standard Mitsunobu protocol that led to a six‐membered ring contraction from ( R,S )‐3,4‐dihydro‐2 H ‐1,5‐benzoxathiepin‐3‐ol via an episulfonium intermediate. The signal ∼ δ =151 ppm, which corresponds to the C4′ carbon atom, is unequivocal proof of the N9′ regioisomer. The potential of the target molecules as anticancer agents is reflected in their activity against the MCF‐7 cancer cell line. The most active compounds have IC 50 values of (6.18±1.70) and (8.97±0.83) μ M . The results indicate that the anticancer activity for the most active compounds is correlated with their capacity to induce apoptosis.